Carboxymethyl cellulose acetate butyrate (CMCAB) has gained increasing importance in several fields, particularly in coating technologies and pharmaceutical research. CMCAB is synthesized by esterification of CMC sodium salt with acetic and butyric anhydrides. CMCAB mixed esters are relatively high molecular weight (MW) thermoplastic polymers with high glass transition temperatures (Tg). CMCAB ester is dispersible in water and soluble in a wide range of organic solvents, allowing varied opportunity to the solvent choice. It makes application of coatings more consistent and defect-free. Its ability to slow down the release rate of highly water-soluble compounds and to increase the dissolution of poorly soluble compounds makes CMCAB a unique and potentially valuable tool in pharmaceutical and amorphous solid dispersions (ASD) formulations. 1. Introduction Cellulose is the most abundant regenerated biopolymer in the planet, with annual production of about 5 × 1011 metric tons. Most of the cellulose is utilized in industry as a raw material in paper production. Only about 4 from 108 million tons of annually produced pulp are used for chemical production [1]. Hydroxyl groups of cellulose can be reacted to form esters or ethers of different physical and chemical properties suitable for various applications [2]. Cellulose derivatives have significant roles in industry; they represent a main source for fibers, textiles, coatings, thermoplastic films, food additives [1], and pharmaceutical technologies [3]. Cellulose derivatives are usually classified as two main classes, esters and ethers, according to the reactant nature. Cellulose derivatives usually contain free hydroxyl groups available for additional treatments to yield mixed esters. The mixed esters have several improved properties over all neat esters. Cellulose acetate propionate (CAP) and cellulose acetate butyrate (CAB) are the most commercially important mixed esters [4]. Mixed cellulose derivatives with both ester and ether groups could be also attained. Due to their low degree of substitution and high hydrolytic stability, carboxymethyl cellulose can be further esterified with organic acid anhydrides to add either single or mixed ester groups [5]. Cellulose esters in coating compositions improved many properties as hardness, aluminum flake orientation, flow and leveling, redissolving resistance, clarity, and gloss while it reduced dry-to-touch time, cratering, and blocking [6–9]. Mixed cellulose derivatives afford the benefits of conventional cellulose esters with a moderate increase in viscosity
References
[1]
X. Qiu and S. Hu, “‘Smart’ materials based on cellulose: a review of the preparations, properties, and applications,” Materials, vol. 6, no. 3, pp. 738–781, 2013.
[2]
A. Shanbhag, B. Barclay, J. Koziara, and P. Shivanand, “Application of cellulose acetate butyrate-based membrane for osmotic drug delivery,” Cellulose, vol. 14, no. 1, pp. 65–71, 2007.
[3]
J. Shokri and K. Adibkia, “Cellulose-medical, pharmaceutical and electronic applications, chapter 3, application of cellulose and cellulose derivatives,” in Pharmaceutical Industries, pp. 47–66, INTECH Open Science/Open Minds, Rijeka, Croatia, 2013.
[4]
K. Balser, L. Hoppe, T. Eicher et al., “Cellulose esters,” in Ullmann's Encyclopedia of Industrial Chemistry, M. Bohnet, G. Bellussi, J. Bus, B. Cornils, and K. Drauz, Eds., John Wiley & Sons, New York, NY, USA, 2004.
[5]
J. L. Paris, Carboxymethyl cellulose acetate butyrate water-dispersions as renewable wood adhesives [M.S. thesis], Virginia Polytechnic Institute and State University, 2010.
[6]
J. E. Lawniczak, J. Posey-Dowty, K. S. Seo, and K. Walker, “Rheological aspects of carboxymethyl cellulose acetate butyrate (CMCABTM) in waterborne coatings,” Paint and Coatings Industry, vol. 19, no. 6, pp. 28–32, 2003.
[7]
J. D. Posey-Dowty, K. S. Seo, K. R. Walker, and A. K. Wilson, “Carboxymethylcellulose acetate butyrate in water-based automotive paints,” Surface Coatings International Part B: Coatings International, vol. 85, no. 3, pp. 203–208, 2002.
[8]
K. W. McCreight, D. C. Webster, and L. K. Kemp, “Aqueous dispersions of carboxylated cellulose esters, and methods of making them,” Patent Number: US 0203278 A1, 2005.
[9]
M. C. Shelton, A. K. Wilson, J. D. Posey-Dowty, G. A. Kramer, and L. G. R. Perdomo, “Low molecular weight carboxyalkyl cellulose esters and their use as low viscosity binders and modifiers in coating compositions,” Patent EP 1603953 A1, 2007, WO 2004/083254 & US 7,893,138 B2, 2011.
[10]
R. Obie, “Use of carboxymethyl cellulose acetate butyrate as a precoat or size for cellulosic man-made fiber boards,” US Patent No. 0090462, US 7026470, 2006.
[11]
R. T. Obie, “Use of carboxyalkyl cellulose esters, such as carboxymethyl cellulose acetate butyrate, to form aqueous dispersions of hydrophobic materials in water,” Patent Number: WO /030801, 2004.
[12]
M. C. Li, J. D. Posey-Dowty, L. R. Lingerfelt, S. K. Kirk, S. Klein, and K. J. Edgar, “Enhanced dissolution of poorly soluble drugs from solid dispersions in carboxymethyl cellulose acetate butyrate matrices,” in Polysaccharide Materials: Performance by Design, K. J. Edgar, T. Heinze, and T. Liebert, Eds., vol. 1017 of ACS Symposium Series, chapter 5, pp. 93–113, ACS, Washington, DC, USA.
[13]
B. Li, H. Liu, M. Amin, L. A. Wegiel, L. S. Taylor, and K. J. Edgar, “Enhancement of naringenin solution concentration by solid dispersion in cellulose derivative matrices,” Cellulose, vol. 20, no. 4, pp. 2137–2149, 2013.
[14]
H. Namikoshi, “Carboxyalkyl acetyl celluloses, Their salts and a process for the preparation of them,” Patent Number: 4,520,192, 1985.
[15]
J. M. Allen, A. K. Wilson, P. L. Lucas, and L. G. Curtis, “Process for preparing carboxyalkyl cellulose esters,” Patent 5,792,856, 1998.
[16]
J. D. Posey-Dowty, A. K. Wilson, L. G. Curtis, P. M. Swan, and K. S. Seo, “Carboxyallkyl cellulose esters for use in aqueous pigment dispersions,” Patent Number: US 5,994,530, 1999.
[17]
B. Han, D. Zhang, Z. Shao, L. Kong, and S. Lv, “Preparation and characterization of cellulose acetate/carboxymethyl cellulose acetate blend ultrafiltration membranes,” Desalination, vol. 311, pp. 80–89, 2013.
[18]
L. Qiu, Z. Shao, M. Yang et al., “Electrospun carboxymethyl cellulose acetate butyrate (CMCAB) nanofiber for high rate lithium-ion battery,” Carbohydrate Polymers, vol. 96, no. 1, pp. 240–245, 2013.
[19]
Y.-J. Wang and K. Yang, “Enzymatic acetylation of carboxymethyl cellulose by lipases,” in Proceedings of the 87th AACC Annual Meeting, vol. 37, Québec, Canada, 2002.
[20]
D. Klemm and T. Heinze, “Acylation of carboxymethyl cellulose accelerated by 4-dimethylaminopyridine,” Synthetic Communications, vol. 16, no. 12, pp. 1499–1508, 1986.
[21]
J. D. Posey-Dowty, T. L. Watterson, A. K. Wilson, K. J. Edgar, M. C. Shelton, and L. R. Lingerfelt, “Zero-order release formulations using a novel cellulose ester,” Cellulose, vol. 14, no. 1, pp. 73–83, 2007.
[22]
J. Amim Jr., D. F. S. Petri, F. C. B. Maia, and P. B. Miranda, “Solution behavior and surface properties of carboxymethyl cellulose acetate butyrate,” Cellulose, vol. 16, no. 5, pp. 773–782, 2009.
[23]
S.-Y. Lv, Z.-Q. Shao, F.-J. Wang, W.-J. Wang, and Y.-H. Li, “Rheological properties of carboxymethyl cellulose acetate butyrate water dispersions,” Polymeric Materials Science and Engineering, vol. 26, no. 8, pp. 54–57, 2010.
[24]
D. Eggers and L. R. Dillard, “Recent developments for carboxymethyl cellulose acetate butyrate in waterborne coatings,” in Proceedings of the 229th ACS National Meeting, San Diego, Calif, USA, March 2005.
[25]
K. R. Walker, “Aqueous coatings composition containing cellulose mixed ester and amine neutralized acrylic resin and the process for the preparation thereof,” Patent Number: US 5,286,768, 1994.
[26]
C. M. Kuo, L. G. Curtis, and P. L. Lucas, “Aqueous dispersion useful in coatings containing hydrolyzed cellulose ester and acrylic resin,” Patent No. 5334638, 1994.
[27]
J. M. Allen, A. K. Wilson, P. L. Lucas, and L. G. Curtis, “Carboxyalkyl cellulose esters,” Patent Number: US 5668273 A, 1997.
[28]
M. Yamaguchi and K. Masuzawa, “Transparent polymer blends composed of cellulose acetate propionate and poly(epichlorohydrin),” Cellulose, vol. 15, no. 1, pp. 17–22, 2008.
[29]
H. Wiese, “Characterization of aqueous polymer dispersions,” in Polymer Dispersions and their Industrial Applications, D. Urban and K. Takamura, Eds., pp. 41–73, Wiley-VCH, Weinheim, Germany, 2002.
[30]
B. L. Wadey, “Plasticizers,” in Encyclopedia of Physical Science and Technology, A. M. Robert, Ed., pp. 441–456, Academic Press, New York, NY, USA, 2001.
[31]
J. Amim Jr., Y. Kawano, and D. F. S. Petri, “Thin films of carbohydrate based surfactants and carboxymethyl cellulose acetate butyrate mixtures: morphology and thermal behavior,” Materials Science and Engineering C, vol. 29, no. 2, pp. 420–425, 2009.
[32]
B. Li, K. Harich, L. Wegiel, L. S. Taylor, and K. J. Edgar, “Stability and solubility enhancement of ellagic acid in cellulose ester solid dispersions,” Carbohydrate Polymers, vol. 92, no. 2, pp. 1443–1450, 2013.
[33]
B. Li, S. Konecke, K. Harich, L. Wegiel, L. S. Taylor, and K. J. Edgar, “Solid dispersion of quercetin in cellulose derivative matrices influences both solubility and stability,” Carbohydrate Polymers, vol. 92, no. 2, pp. 2033–2040, 2013.
[34]
B. Li, S. Konecke, L. A. Wegiel, L. S. Taylor, and K. J. Edgar, “Both solubility and chemical stability of curcumin are enhanced by solid dispersion in cellulose derivative matrices,” Carbohydrate Polymers, vol. 98, no. 1, pp. 1108–1116, 2013.
[35]
A. L. Gomes, G. V. Rodrigues, and M. C. Goncalves, “Preparation of poly (3-hydroxybutyrate)/carboxymethyl cellulose acetate butyrate blends using gel formation,” in Proceedings of the 10th Brazilian Congress on Polymers, pp. 1–6, Sao Paulo, Brazil, 2009.
[36]
L. Xie, Z. Shao, W. Wang, and F. Wang, “Superhydrophobicity of CMCAB fibrous mats produced by electrospinning,” Integrated Ferroelectrics, vol. 135, no. 1, pp. 55–61, 2012.
[37]
L. S. Blachechen, M. A. Souza, and D. F. S. Petri, “Effect of humidity and solvent vapor phase on cellulose esters films,” Cellulose, vol. 19, no. 2, pp. 443–457, 2012.
[38]
M. A. El-Taraboulsi, M. A. Mandil, and H. E.-S. M. Ali, “Reverse osmosis studies on desalination membranes formed from chemically modified cellulose acetate,” Carbohydrate Research, vol. 13, no. 1, pp. 83–88, 1970.
[39]
G. Broze, “Acetylated sugar ethers as bleach activators and detergency boosters,” Patent No. 4889651, 1989.
[40]
J. Amim Jr. and D. F. S. Petri, “Effect of amino-terminated substrates onto surface properties of cellulose esters and their interaction with lectins,” Materials Science and Engineering C, vol. 32, no. 2, pp. 348–355, 2012.
